126222-05-7Relevant academic research and scientific papers
Structures and Reactivities of New Dolabellane Diterpenoids from the Caribbean Gorgonian Eunicea laciniata
Shin, Jongheon,Fenical, William
, p. 3392 - 3398 (1991)
Five new diterpenoids of the dolabellane class (3-7) have been isolated from the Caribbean gorgonian Eunicea laciniata Duchassaing and Michelotti.The structures of these metabolites were defined by combined spectra and chemical methods.The conformation and reactivity of the 11-membered ring of the dolabellanes was investigated by 1H NMR nuclear Overhauser enhancement difference spectroscopy (NOEDS) and by selected chemical transformations involving transannular cyclizations.
Concise total syntheses of palominol, dolabellatrienone, β-araneosene, and isoedunol via an enantioselective Diels-Alder macrobicyclization
Snyder, Scott A.,Corey
, p. 740 - 742 (2007/10/03)
Concise total syntheses of four members of the dolabellane family of diterpenoid natural products are reported. Key features of the developed route include the first demonstration of an enantioselective, intramolecular Type I Diels-Alder macrobicyclization, the first example of a stereoselective π-allyl Stille coupling reaction involving a farnesyl-derived intermediate, a powerful new reagent for the formation of dithianes with acid-sensitive molecules, and a unique and highly efficient ring-contraction sequence based on a modified Wolff photochemical rearrangement. Copyright
Total synthesis of the dolabellane marine diterpenoids, claenone, palominol and dolabellatrienone
Miyaoka, Hiroaki,Isaji, Yutaka,Mitome, Hidemichi,Yamada, Yasuji
, p. 61 - 76 (2007/10/03)
The synthesis of marine dolabellane diterpenoids claenone, palominol and dolabellatrienone was conducted from D-mannitol. In each case, formation of the bicyclo[2.2.1]heptane derivative by sequential Michael reaction, preparation of the tetrasubstituted c
